30 best episodes of Whose Line is it Anyway?

Written by:
August 29, 2019

30 best episodes of 'Whose Line is it Anyway?'

"Whose Line is it Anyway?" is the show where "everything's made up and the points don't matter." The series, adapted from the British show, brought improvisational comedy to American audiences in 1998 and has been cracking us up ever since. The original version of the American show was hosted by comedian and sitcom star Drew Carey, who convinced ABC to give it a chance, and featured Ryan Stiles, Colin Mochrie, and Wayne Brady, alums from the British version. They performed alongside a rotating guest performer, with familiar faces like Stephen Colbert, Whoopi Goldberg, and Robin Williams joining in on the fun. The show ran from 1998 to 2007 and was revived in 2013 with the same original cast. Comedian Aisha Tyler took over the host's chair, and the show still includes a celebrity guest each week.

These guests join the cast in improvisational games, some of which require audience participation. In "Scenes from a Hat," the audience contributes funny scenarios pulled from a hat at random. In others, like "Party Quirks" or "Let's Make a Date," three performers are pre-assigned roles that the fourth has to guess: are they guests at the host's party, contestants on a dating show, or something completely different? Other popular games include "Hoedown" (each participant sings an improvised verse in a hoedown-style song), "Greatest Hits" (with cast member Wayne Brady performing songs from an album made up by two other contestants), and "Film, TV and Theatre Styles" (with two performers given a scene and several different film styles to perform).

Altogether, there are 14 seasons and 339 episodes of bizarre, hilarious, and entirely improvised comedy, which can be overwhelming when you're trying to figure out where to start. Stacker compiled a list of the best 30 episodes of "Whose Line is it Anyway," based on IMDb user ratings. Episodes from Drew Carey's years hosting (1998 to 2007) as well as Aisha Tyler's (2013 to the present) were considered; each episode required a minimum of 30 IMDb user votes as of August 2019 to be ranked. Ties were broken in favor of the episode with the most votes.

Whether you're a longtime fan or just looking for a laugh, read on to discover the best episodes of "Whose Line is it Anyway?"

You may also like: Best 'Simpsons' episodes of all time

#30. Show No. 210

- Season 2, Episode 19
- IMDb rating: 7.7
- IMDb votes: 30
- Air date: Jan. 13, 2000

This episode featured frequent recurring guest Greg Proops—comedian and voice actor in “Bob the Builder” who has appeared on the show 70 times—alongside Colin Mochrie, Wayne Brady, and Ryan Stiles. This episode marked the return of “Questionable Impressions,” a game where performers only speak in questions and use a different impression every time they re-enter the scene. The cast members and Proops also played “Scenes from a Hat,” “Weird Newscasters,” and “Three-Headed Broadway Star,” and closed out the episode with a puberty-themed “hoedown” alongside host Drew Carey.

#29. Mary Killman and Mariya Koroleva

- Season 1, Episode 5
- IMDb rating: 7.8
- IMDb votes: 30
- Air date: July 30, 2013

Olympic synchronized swimmers Mary Killman and Mariya Koroleva and guest comedian Jeff Davis (who’s appeared on the show 40 times) joined Wayne Brady, Colin Mochrie, and Ryan Stiles in the first season of the revived show. The four comedians gave their take on an escape movie while playing “Hollywood Director” (shedding some clothes in the process) and acted out a skiing mishap in “Forward/Reverse.” Mochrie, Brady, and Davis performed an entire scene sideways, Koroleva and Killman acted as props for Stiles and Mochrie in “Living Scenery,” and danced along to Davis and Brady’s boy band-style “Duet.”

#28. Show No. 220

- Season 2, Episode 5
- IMDb rating: 7.8
- IMDb votes: 30
- Air date: Oct. 8, 1999

Comedian, country singer, and actor Charles “Chip” Esten, who played Deacon Claybourne in “Nashville,” joined the regular cast for this episode—one of more than 40 appearances on the show during both runs. During the episode, Mochrie and Stiles recreated a scene from “Gone With the Wind” in the audience-generated game “Whose Line?” and all four performers sang a “Hoedown.” They also played “Weird Newscasters,” “Duet,” “Scenes from a Hat,” and “Questions Only.”

#27. Show No. 225

- Season 2, Episode 18
- IMDb rating: 7.8
- IMDb votes: 32
- Air date: Jan. 6, 2000

Game show host Brad Sherwood was the second most-featured guest in the show’s history after Greg Proops, appearing in 69 episodes. In this episode, the crew teamed up to deal with a mosquito crisis in “Superheroes,” raised money for sitcom stars in a game of “Telethon,” and also played “Film, Theatre and TV Styles,” “Song Titles,” “Sound Effects,” and “Three-Headed Broadway Star.”

#26. Show No. 113

- Season 1, Episode 11
- IMDb rating: 7.8
- IMDb votes: 48
- Air date: Jan. 13, 1999

Highlights of this episode included recurring guest Greg Proops’ Bill Clinton impression, as well as Wayne Brady singing about postal workers in “Greatest Hits.” The cast also played “Dating Service Videos,” and rounded out the episode with “Film, Theatre, and TV Styles,” “Weird Newscasters,” and “Helping Hands” with host Drew Carey.

#25. Show No. 101

- Season 1, Episode 4
- IMDb rating: 7.8
- IMDb votes: 61
- Air date: Aug. 26, 1998

Brad Sherwood joins the crew in rapping about meeting someone in a park. Later, Sherwood plays the host in a game of “Party Quirks,” and Colin Mochrie pretends to be a skier who can’t stop running into things. Other games in this episode included “Weird Newscasters,” “Duet,” “Animals” “Props,” “Moving People,” and “Foreign Film Dub.”

#24. Show No. 201

- Season 2, Episode 4
- IMDb rating: 7.9
- IMDb votes: 32
- Air date: Oct. 7, 1999

In this episode, Wayne Brady chose between Greg Proops’ exorcist, Ryan Stiles’ club bouncer, and Colin Mochie’s fanatic Canadian hockey player during “Let’s Make a Date.” Other games featured in the episode included “Film Dub,” “Three-Headed Broadway Star,” “Film, Theatre, and TV Styles,” “Greatest Hits,” and “World's Worst.”

#23. Misha Collins

- Season 2, Episode 13
- IMDb rating: 7.9
- IMDb votes: 33
- Air date: June 16, 2014

Misha Collins took a break from fighting evil on the CW’s “Supernatural” to join the second season of the “Whose Line” revival. He became the subject of a “Duet” by Wayne Brady and recurring guest Brad Sherwood (in Russian folk style) and pretended to be “Living Scenery” for two friends’ motorcycle trip to Las Vegas. Sherwood acted as the fourth man in the rest of the episode’s games, “Let's Make a Date,” and “Scenes from a Hat,” and finished off the episode with a cheese-themed “Hoedown.”

#22. Show No. 206

- Season 2, Episode 3
- IMDb rating: 7.9
- IMDb votes: 33
- Air date: Sep. 30, 1999

As the episode’s winner, veteran guest Greg Proops looked on with delight as Drew Carey joined the cast in a “Hoedown” about the Village People (known for their hit “YMCA”). The cast also played “Weird Newscasters,” “African Chant,” “Scenes from a Hat,” “Change Emotion,” and a round of “Greatest Hits” featuring an exterminator.

#21. Show No. 209

- Season 2, Episode 1
- IMDb rating: 7.9
- IMDb votes: 38
- Air date: Sep. 16, 1999

The second season of the original American series opened with Wayne Brady officially joining the regular cast. Featuring frequent guest performer Chip Esten as the episode’s fourth participant, the cast performed a song about lumberjacks in love during “Three-Headed Broadway Star,” and played “Let's Make a Date,” “Props,” “Stand Sit Lie Down,” “Greatest Hits,” and “Hoedown.”

#20. Show No. 102

- Season 1, Episode 6
- IMDb rating: 7.9
- IMDb votes: 64
- Air date: Sep. 9, 1998

Aired before Wayne Brady joined the regular cast, this episode featured guest performers Brad Sherwood and actress Kathy Kinney, (“The Drew Carey Show” and “Newhart”) in her first and only appearance on the show. Kinney played the distressed mother of the “three little pigs” during a game of “Daytime Talk Show” in one of the episode’s stand-out moments. The cast also played “Let's Make a Date,” “Sound Effects,” “Props,” “Helping Hands,” “Hoedown,” and “90-Second Alphabet.”


#19. Show No. 232

- Season 2, Episode 29
- IMDb rating: 8.0
- IMDb votes: 30
- Air date: March 23, 2000

Colin Mochrie and Ryan Stiles played two secret agents on an “Improbable Mission” to do laundry for a visiting dignitary. Mochrie’s repeated use of “the cat!” to solve the mission’s problems has long made it one of the show’s most enduring sketches. Greg Proops contributed to “Let's Make A Date,” “Song Styles,” “Party Quirks,” and “Three-Headed Broadway Star.”

#18. Show No. 213

- Season 2, Episode 14
- IMDb rating: 8.0
- IMDb votes: 31
- Air date: Nov. 25, 1999

This episode marked the debut of “The Millionaire Show,” a parody of “Who Wants to Be a Millionaire?” In another highlight, the audience participated in a song about toothbrushes created by Stiles, Wayne Brady, and guest comedian Brad Sherwood. The cast also played “Superheroes,” “Film, Theatre and TV Styles,” “Props,” “Motown,” and finished up with a “Hoedown” about family reunions.

#17. Show No. 114

- Season 1, Episode 14
- IMDb rating: 8.0
- IMDb votes: 46
- Air date: Feb. 3, 1999

Ian Gomez—known for his roles on the “Drew Carey Show,” “Felicity,” and “Cougar Town”—joined regular guest Brad Sherwood for one of his two appearances on “Whose Line is it Anyway?” Gomez played a hybrid sportscaster/fed-up Ricky Ricardo during a “Weird Newscasters” segment. Other games featured in this episode were “Let's Make A Date,” “Moving People,” “Greatest Hits,” “Party Quirks,” and “Helping Hands.”

#16. Show No. 119

- Season 1, Episode 12
- IMDb rating: 8.0
- IMDb votes: 50
- Air date: Jan. 20, 1999

Wayne Brady and Brad Sherwood took to the stage to participate in a game of “Telethon” to benefit NBA players. A game of “Film, Theatre, and TV Styles” was another highlight: Brady and Stiles recreated the biopic “Birdman of Alcatraz” in the styles of Shakespeare, sumo wrestling, and adult film. The cast also played “Let's Make A Date,” “Duet,” “Newsflash,” and “Hoedown.”

#15. Show No. 103

- Season 1, Episode 1
- IMDb rating: 8.0
- IMDb votes: 102
- Air date: Aug. 5, 1998

The American version of “Whose Line is it Anyway?” kicked off with the show’s most frequent guest, Greg Proops, guessing his castmates’ strange “Party Quirks.” The episode started off with Ryan Stiles infamously portraying the birth of a foal. The rest of the episode—which included “Let's Make a Date,” “Sound Effects,” “Hats,” “Greatest Hits,” and “Foreign Film Dub”—wasn’t quite as bizarre, but still managed to start the series with a bang.

#14. Show No. 205

- Season 2, Episode 2
- IMDb rating: 8.1
- IMDb votes: 34
- Air date: Sep. 23, 1999

Recurring guest Brad Sherwood joined Drew Carey, Ryan Stiles, and Colin Mochie to serenade Wayne Brady (the episode’s “winner”) with a “Hoedown” about drinking too much. The performers also worked their way through “Weird Newscasters,” “Duet,” “Newsflash,” “Party Quirks,” and “Scenes from a Hat.”

#13. Candice King

- Season 1, Episode 3
- IMDb rating: 8.1
- IMDb votes: 46
- Air date: July 23, 2013

Candice King, best-known for her role as Caroline Forbes on the supernatural drama “The Vampire Diaries” and its spinoff “The Originals,” was featured in this episode. King was the subject of a Latin pop song by Wayne Brady during “Song Styles” and joined “Living Scenery” alongside two mountaineers climbing Mount Everest. This episode also marked the first appearance of actor and comedian Keegan-Michael Key, of “Key & Peele” and “MAD TV,” who has appeared on the show nine times. Key contributed to the rest of the episode’s games: “Hollywood Director,” “Props,” and “Dating Profiles.”

#12. Show No. 111

- Season 1, Episode 8
- IMDb rating: 8.1
- IMDb votes: 55
- Air date: Dec. 9, 1998

Denny Siegel, a correspondent on “The Daily Show,” made her first of 14 “Whose Line” appearances in this episode. Siegel took on the role of host in “Party Quirks” and a bachelorette in search of a partner on “Let’s Make a Date.” “Props,” a game of “Song Styles” about swimming lessons, the “Greatest Hits” of butchers everywhere, and “Helping Hands” rounded out the episode.

#11. Show No. 117

- Season 1, Episode 10
- IMDb rating: 8.1
- IMDb votes: 57
- Air date: Jan. 6, 1999

Denny Siegel returned for her second guest appearance to open the show with a melodramatic teen soap opera in “Questions Only.” Wayne Brady’s gospel-style song about an immigration attorney in “Song Styles” marked another highlight in this episode. The four comedians also played “Newsflash,” “Sound Effects,” “Weird Newscasters,” “Scene to Rap,” and “Hoedown.”

#10. Show No. 204

- Season 2, Episode 10
- IMDb rating: 8.2
- IMDb votes: 30
- Air date: Nov. 5, 1999

Drew Carey joined Wayne Brady and Ryan Stiles in “Three-Headed Broadway Star” for the very first time, accidentally singing an entire line instead of just one word during “You’ve Got Sole” from made-up Broadway musical “My Favorite Shoe.” Other highlights included Greg Proops teaming up with the regular cast as “Superheroes” who have run out of deodorant, and Wayne Brady impersonating an aging Michael Jackson in “Song Styles.” The cast also played “Newsflash,” “Questionable Impressions,” and “Dating Service Video.”

#9. Show No. 227

- Season 2, Episode 22
- IMDb rating: 8.2
- IMDb votes: 31
- Air date: Feb. 4, 2000

In this episode, Colin Mochrie and Ryan Stiles acted out a film noir scene in a fast food restaurant during a game of “Narrate.” The scene famously ended with the two longtime collaborators kissing on-screen. Canadian actress and frequent series guest Kathy Greenwood played a woman dining with a colleague in a war zone during “Themed Restaurant,” and portrayed a bratty granddaughter in “Weird Newscasters.” The episode finished up with a racy singing telegram in “Song Styles,” after the cast played “Scenes From A Hat,” and sang a Halloween-themed “Hoedown.”

#8. Wilson Bethel

- Season 1, Episode 6
- IMDb rating: 8.2
- IMDb votes: 38
- Air date: Aug. 6, 2013

Actor Wilson Bethel, from the CW’s “Hart of Dixie” and Netflix's “Daredevil” appeared on this episode of “Whose Line is it Anyway?” Bethel was serenaded with a Motown-style “Duet” by Wayne Brady and frequent show guest Gary Anthony Williams, an actor and comedian known for roles in “Boston Legal” and “Harold and Kumar Go to White Castle.” Bethel also joined in for the three-headed song "I Can't Live Without Your Rubber Ducky.” Other games featured in the episode are “Helping Hands,” “Sideways Scenes,” and “Weird Newscasters.”

#7. Kevin McHale

- Season 1, Episode 2
- IMDb rating: 8.2
- IMDb votes: 49
- Air date: July 16, 2013

“Whose Line is it Anyway” launched its first season after a six-year hiatus by bringing on several new celebrity guests, including Kevin McHale of hit TV show “Glee.” Former “Saturday Night Live” writer Heather Anne Campbell also contributed to games of “Scenes from a Hat,” “Song Styles,” “Dubbing,” “Sideways Scene,” and “Helping Hands.”

#6. Lauren Cohan

- Season 1, Episode 1
- IMDb rating: 8.2
- IMDb votes: 64
- Air date: July 16, 2013

Lauren Cohan, from FX’s “The Walking Dead,” was the inaugural guest on the revival of “Whose Line is it Anyway?” acting out a zombie apocalypse in “Dubbing” and playing a prop in “Living Scenery.” Actor and comedian Gary Anthony Williams also made his “Whose Line” debut on the new version of the show, participating in “Let's Make a Date,” “Dubbing,” “What's in the Bag,” and “Scenes from a Hat.” He’s since appeared in 22 episodes.

#5. Show No. 239

- Season 2, Episode 39
- IMDb rating: 8.3
- IMDb votes: 31
- Air date: May 18, 2000

Chip Esten and Wayne Brady teamed up for “Duet,” serenading a sandwich shop employee. Drew Carey joined in for “Foreign Film Dub,” translating a film into “Canadian.” In one of the show’s best-known “Newsflash” segments, Colin Mochrie reported in front of a green screen flashing pictures of himself, and kicked off the segment by claiming that "it all started with a badly timed bald joke,” without realizing the context. “Song Titles” and a “Hoedown” about plastic surgery rounded out this episode.

#4. Show No. 8016

- Season 8, Episode 16
- IMDb rating: 8.4
- IMDb votes: 31
- Air date: Nov. 10, 2006

Greg Proops joined this episode, playing a game of “Superheroes” in which the four performers formed an odd band of heroes facing off against a global beer crisis. The episode also featured “Sound Effects,” “Props,” “Hey You Down There,” “Daytime Talk Show,” “Scene to Rap,” and “Hats.”

#3. The Best of Whose Line Is It Anyway?

- Season 3, Episode 0
- IMDb rating: 8.8
- IMDb votes: 32
- Air date: Oct. 4, 2000

This clip show that aired just before the show’s third season featured host Drew Carey introducing some of the first two seasons’ most memorable moments. It also presented a number of bloopers and outtakes from the show that didn’t make it to air.

#2. Show No. 313

- Season 3, Episode 9
- IMDb rating: 8.8
- IMDb votes: 66
- Air date: Nov. 16, 2000

Robin Williams’ sole appearance on “Whose Line is it Anyway” gave the comic legend a chance to show off his considerable improv skills. He joined the regulars for “Film Director” (featuring "Riverdance"), sang gospel during “Duet,” played a fashion-conscious party guest during “Party Quirks,” and participated in “Scenes From A Hat” and “Props.”

#1. Show No. 521

- Season 5, Episode 17
- IMDb rating: 9.2
- IMDb votes: 76
- Air date: June 20, 2003

Regular guest performer Greg Proops (who appeared in 70 episodes) joined the cast for “Multiple Personalities” and “Newsflash,” both of which featured jokes about flamboyant celebrity fitness personality Richard Simmons. Simmons himself later surprised the cast and audience to great effect, participating in “Song Styles,” “Living Scenery,” and “Moving People.” Simmons’ appearance in “Living Scenery” is considered one of the most infamous scenes in the entire series, due to his exaggerated signature racy gestures.

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